Morpholine → HCID 9921081, compound

HRID 2086932Notes

Reaction equation

HRID 2086932 reaction equation
C([C:4]1[CH:8]=[CH:7][S:6]C=1)(=O)C.[S:9]1[CH:13]=[CH:12][C:11]([C:14]([CH2:16][C:17]#[N:18])=[O:15])=[CH:10]1.N1CCOC[CH2:20]1.[S]>CC(=O)CC>[NH2:18][C:17]1[S:6][C:7]([CH3:20])=[C:8]([CH3:4])[C:16]=1[C:14]([C:11]1[CH:12]=[CH:13][S:9][CH:10]=1)=[O:15]

Participants

6

Reactant 4

HCID 8083MorpholineHCID 151161-(Thiophen-3-yl)ethanoneHCID 27400753-Oxo-3-(thiophen-3-yl)propanenitrile2×HCID 5362487Sulfur

Product 1

HCID 9921081HCID 9921081, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure of Example 1 was followed except that 3-acetylthiophene (Aldrich) was used in place of acetophenone to prepare the corresponding 2-(thiophene-3-carbonyl)acetonitrile (Steps A and B). 2-Butanone (Aldrich), 2-(thiophene-3-carbonyl)acetonitrile, morpholine, and sulfur were reacted according to the procedure of Step C, Example 1, to afford the desired compound. Yield: 38%; IR (KBr) cm−1: 3337, 3229, 3107, 1576, 1427, 1265, 1162, 855, 736, 719; 1H NMR (CDCl3):δ1.71 (s, 3H), 2.15 (s, 3H), 6.17 (bs, 2H), 7.30 (d, J=2.2 Hz, 2H), 7.63 (t, 1H, J=2 Hz); yellow solid, mp: 122-123° C. (petroleum ether).

Sources & evidence

ORD record
ord-241087c59362499b83dd56dd215ebe92
Source dataset
uspto-grants-2004_04
Patent number
US06727258B2

Reaction notes

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